Self-assembled nanomedicine of the conjugate based on Ce6 and chrysin improves photodynamic performance

Abstract

Conjugates based on photosensitizer Ce6 and chemotherapeutic drug chrysin, when dispersed into water with DMSO, can rapidly self-assemble into nanoparticles. In Ce6-TEGDM-Chrysin, the two triethylene glycol monomethyl ether (TEGDM) chains enhance molecular polarity and hydrophilicity. Notably, one of the TEGDM chains extends toward the porphyrin ring plane, forming a wrapping configuration that increases steric hindrance to π-π stacking on the molecular plane. As a novel photosensitizer, Ce6-TEGDM-Chrysin exhibits outstanding photophysical properties, with a fluorescence lifetime of 3.10 ns, a fluorescence quantum yield of 18.3 %, and a singlet oxygen quantum yield of 46.2 % in DCM. Compared to Ce6-OMe-Chrysin as well as the co-assembled nanoparticle Ce6@Chrysin of Ce6 and chrysin, Ce6-TEGDM-Chrysin not only demonstrates superior photodynamic activity against melanoma but also exhibits a strong enrichment ability in mouse tumor tissues due to the EPR effect of nanodrugs and the inherent tumor affinity of porphyrins.